N-benzoyl-phenylalanyl-glycine-nitrile

ID: ALA371466

Chembl Id: CHEMBL371466

PubChem CID: 11702265

Max Phase: Preclinical

Molecular Formula: C18H17N3O2

Molecular Weight: 307.35

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Canonical SMILES:  N#CCNC(=O)[C@H](Cc1ccccc1)NC(=O)c1ccccc1

Standard InChI:  InChI=1S/C18H17N3O2/c19-11-12-20-18(23)16(13-14-7-3-1-4-8-14)21-17(22)15-9-5-2-6-10-15/h1-10,16H,12-13H2,(H,20,23)(H,21,22)/t16-/m0/s1

Standard InChI Key:  WEIUVZVWLANUJJ-INIZCTEOSA-N

Alternative Forms

Associated Targets(Human)

CTSS Tchem Cathepsin S (3285 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CTSK Tchem Cathepsin K (3011 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CTSB Tchem Cathepsin B (3822 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CTSL Tclin Cathepsin L (3852 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Papain (844 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CTSL Cathepsin L (58 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Cruzipain (33337 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Trypanosoma cruzi (99888 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
LLC-MK2 (227 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 307.35Molecular Weight (Monoisotopic): 307.1321AlogP: 1.67#Rotatable Bonds: 6
Polar Surface Area: 81.99Molecular Species: NEUTRALHBA: 3HBD: 2
#RO5 Violations: 0HBA (Lipinski): 5HBD (Lipinski): 2#RO5 Violations (Lipinski): 0
CX Acidic pKa: 11.92CX Basic pKa: CX LogP: 1.70CX LogD: 1.70
Aromatic Rings: 2Heavy Atoms: 23QED Weighted: 0.80Np Likeness Score: -0.86

References

1. Löser R, Schilling K, Dimmig E, Gütschow M..  (2005)  Interaction of papain-like cysteine proteases with dipeptide-derived nitriles.,  48  (24): [PMID:16302809] [10.1021/jm050686b]
2. Wammes AE, Hendriks TG, Amatdjais-Groenen HI, Wijdeven MA, van Hest JC, van Delft FL, Ritschel T, Rutjes FP..  (2014)  Influence of azide incorporation on binding affinity by small papain inhibitors.,  22  (20): [PMID:24972724] [10.1016/j.bmc.2014.06.001]
3. Schmitz J, Li T, Bartz U, Gütschow M..  (2016)  Cathepsin B Inhibitors: Combining Dipeptide Nitriles with an Occluding Loop Recognition Element by Click Chemistry.,  (3): [PMID:26985300] [10.1021/acsmedchemlett.5b00474]
4. Bonatto, Vinicius, Batista, Pedro Henrique Jatai, Cianni, Lorenzo, De Vita, Daniela, Silva, Daniel G., Cedron, Rodrigo, Tezuka, Daiane Y., de Albuquerque, Sergio, Moraes, Carolina Borsoi, Franco, Caio Haddad, Lameira, Jeronimo, Leitao, Andrei, Montanari, Carlos A..  (2020)  On the intrinsic reactivity of highly potent trypanocidal cruzain inhibitors,  11  (11): [PMID:34095840] [10.1039/d0md00097c]
5. Ribeiro JFR,Cianni L,Li C,Warwick TG,de Vita D,Rosini F,Dos Reis Rocho F,Martins FCP,Kenny PW,Lameira J,Leitão A,Emsley J,Montanari CA.  (2020)  Crystal structure of Leishmania mexicana cysteine protease B in complex with a high-affinity azadipeptide nitrile inhibitor.,  28  (22): [PMID:33038787] [10.1016/j.bmc.2020.115743]
6. Rocha DA, Silva EB, Fortes IS, Lopes MS, Ferreira RS, Andrade SF..  (2018)  Synthesis and structure-activity relationship studies of cruzain and rhodesain inhibitors.,  157  [PMID:30282318] [10.1016/j.ejmech.2018.08.079]

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